Probing disaccharide selectivity with modular fluorescent sensors

被引:33
作者
Arimori, S [1 ]
Phillips, MD [1 ]
James, TD [1 ]
机构
[1] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England
基金
英国工程与自然科学研究理事会;
关键词
disaccharide; recognition; fluorescence sensor; boronic acid;
D O I
10.1016/j.tetlet.2003.12.013
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Six modular photoinduced electron transfer (PET) sensors bearing two phenylboronic acid receptors have been evaluated as fluorescent disaccharide sensors. The length of linker separating the two boronic acid moieties was varied and the sensors' interaction with disaccharides assessed via fluorescence spectroscopy. It was shown that saccharide selectivity was influenced by the choice of linker length. Diboronic acid sensors 3(n) also displayed significant specificity for the disaccharides linked to the carbon on the 3rd or 6th position (as numbered from the anomeric centre) over those linked at the 4th position. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1539 / 1542
页数:4
相关论文
共 31 条
[11]   Cinderella's coach is ready [J].
Hurtley, S ;
Service, R ;
Szuromi, P .
SCIENCE, 2001, 291 (5512) :2337-2337
[12]   Meso-meso-linked porphyrin dimer as a novel scaffold for the selective binding of oligosaccharides [J].
Ikeda, M ;
Shinkai, S ;
Osuka, A .
CHEMICAL COMMUNICATIONS, 2000, (12) :1047-1048
[13]  
James TD, 2002, TOP CURR CHEM, V218, P159
[14]   Selective detection of D-lactulose by a porphyrin-based diboronic acid [J].
Kijima, H ;
Takeuchi, M ;
Shinkai, S .
CHEMISTRY LETTERS, 1998, (08) :781-782
[15]  
Lecollinet G, 2002, ANGEW CHEM INT EDIT, V41, P4093, DOI 10.1002/1521-3773(20021104)41:21<4093::AID-ANIE4093>3.0.CO
[16]  
2-I
[17]   POLYOL COMPLEXES AND STRUCTURE OF THE BENZENEBORONATE ION [J].
LORAND, JP ;
EDWARDS, JO .
JOURNAL OF ORGANIC CHEMISTRY, 1959, 24 (06) :769-774
[18]   Construction of artificial signal transducers on a lectin surface by post-photoaffinity-labeling modification for fluorescent saccharide biosensors [J].
Nagase, T ;
Nakata, E ;
Shinkai, S ;
Hamachi, I .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (15) :3660-3669
[19]   Boronic acids as fructose sensors. Structure determination of the complexes involved using (1)J(CC) coupling constants [J].
Norrild, JC ;
Eggert, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1996, (12) :2583-2588
[20]   EVIDENCE FOR MONODENTATE AND BISDENTATE BORONATE COMPLEXES OF GLUCOSE IN THE FURANOSE FORM - APPLICATION OF (1)J(C-C)-COUPLING-CONSTANTS AS A STRUCTURAL PROBE [J].
NORRILD, JC ;
EGGERT, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (05) :1479-1484